Dating and Mating Advice for Singles Over 50

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Dating Advice Over 50

Before you move into actively seeking a mate or a date it’s good, as my colleague Christine points out, to ask why would I start dating?

Many men and women I’ve met feel some kind of peer pressure to be a couple. Women, in particular, voice the concern that they will not be invited to social gatherings if they show up single. I have enough anecdotal evidence to convince me this really does happen. Single men, on the other hand, are sought out eagerly to fill empty seats at dinner. I can’t explain it.

Men I know, and some women too, want to feed a hunger for sex. That’s a powerful urge, one not easily satisfied. I get it.

So there are many reasons to seek a partner and I agree with Christine’s analysis posted here earlier in every particular.

But let me offer some ideas why you should NOT be dating.

You really like a lot of time alone. Reading books, writing, watching TV. It’s much easier if you don’t have think about someone else and the time you SHOULD be spending with them. Not everyone is equally social and some of us just aren’t social at all. We are loners. That’s not the same as lonely.

You don’t negotiate well. You have your ways of doing and being and really don’t want to change. What you eat, how you eat. What you talk about or don’t. Politics. Religion. If you’re set in concrete in your attitudes and actions you may not be a good candidate for a partnership.

You don’t have time or energy to work at dating. Finding a romantic partner is like looking for a job. You have to persist, organize and accept rejection. Unless you are truly committed, you will only suffer frustration.

You aren’t really over a previous relationship. Jumping in too early will not turn out well. It can take years to get over a failed relationship. One measure I like is how often do you miss that previous relationship or get angry about it. If you can’t go more than a week without angst about the past, you probably aren’t ready.

Which is to say there may be good reasons for you NOT to date. My recommendation, only get started if you’re sure you’re ready and willing to invest the time and emotional energy required.

So, now that we’re into the month of February. . . how are you feeling about your New Year’s resolutions?

Resolutions are another way of creating important boundaries in your life. You might even consider creating resolutions throughout the year (not just at the beginning). Bottom line – when something becomes a big enough problem and you truly want a change, this is the time to make a resolution.

The tricky part of all resolutions is – how you do you make one that sticks? I’ve found these five points to be quite helpful:

Be convinced it will make your life better.

Break it into very small goals, and clearly state each goal.

Be accountable to yourself and at least one other person.

Be your own cheerleader, and have at least one other cheerleader.

Be able to adjust your expectations when necessary.

In this post, let’s just talk about point 1:

*Be convinced it will make your life better.*

With any resolution, it’s important to make sure you’re honest with yourself about the underlying reason. For example, let’s say your resolution is to start actively dating (and find a partner). In this case, you’d need to ask yourself – why do I want to start dating?

Let’s suppose your answer to this is – you’re lonely. You want to find a partner so you won’t be lonely anymore… you’ll have someone to go places with and someone to talk to.

Are you convinced that dating (and finding a partner) will make your life better? Will it solve your loneliness? To answer this second question, you might have to dig a little deeper.

Why are you lonely? How did you end up feeling this way?

Will dating (and finding a partner) automatically solve your loneliness? Is it as simple as having someone at the movies or at the dinner table? Or is there something deeper going on with you?

There are lots of possible answers to these questions.

I’ve seen cases where it really was that simple – having a partner took care of the loneliness because the woman (or man) had done work on themselves before they dated.

Alternatively, I’ve coached men and women who came to me because – they previously had found a partner – and were surprised to find themselves still lonely while in the relationship!

Some of my clients have learned through coaching they need to make friends with themselves first. This leads them to finding they enjoy their own company, and that by itself reduces loneliness. And there’s a bonus to this one: (1) Once you know and like yourself better, you’re also much better prepared to find the right partner for your personality and needs and (2) befriending yourself can help you feel less needy and desperate about meeting someone, which can in turn lead you to meet other singles who also don’t feel needy or desperate.

Other clients found they needed to enlarge their circle of friends before doing the hard work and taking the risk of dating. Creating a support system around yourself can help you feel more confident and comfortable about dating. And making new friends will open doors to new things and new people.

Does your resolution this year involve dating? Or something else? How convinced are you that it will make your life better? What are you willing to do to make this resolution a reality? Let us know. We’d love to hear from you.

Joel: I know, I know, “shop for women” is… off putting. But that’s the best term I can think of. (Your suggestions welcome.) Point being… I look for certain things and I suspect most men do. Crafting your online profile so it creates appeal for the REAL you is one element that will help you succeed.

For me, a major factor is cheerfulness. Does her text and photos convey a happy person? That certainly includes smiling photos. I remember a few that actually looked like the woman was scowling, even angry. I wondered why she posted it.

I also look for women who have pictures of themselves in ordinary situations, without makeup, in casual clothes, exercise clothes (yoga pants welcome!), gardening…. whatever. I conclude a woman who posts unbeautiful pictures has confidence and is happy with herself. What will you post to convey that about yourself?

Christine: I think shopping is the perfect term! In fact, I’ve often said to female clients: Think about looking for and interviewing potential dates (especially when using online dating) as “shopping for men”.

And here’s why:

Shopping is often a pleasurable activity for women.

Shopping often feels leisurely and calm.

Shopping means we have lots of choices.

Shopping includes trying out a variety of options so we can compare and contrast to see exactly how we feel about each one.

And finally, each of these elements is a good way to bring our authentic selves along (which is essential for successful dating).

Sometimes when we go shopping, we have a clear idea of what we’re looking for. However, we may need to “try things on” to help us decide what we really want. Dating is no different. Just like shopping, you can start out with a list of what you think you’d like and then make adjustments as you “try out options”.

If you can start to look at dating this way, your attitude is likely to be much more relaxed. Many women tell me that dating is “too much work”. In contrast, many women say they enjoy shopping and don’t consider it work.

So, with a slight shift of attitude, shopping for men just might become a fun and interesting activity for you.

My message today isn’t about New Year’s resolutions. It’s about truly focusing on what would make you happy and then taking small steps each day toward that happiness.

I believe people can make a list that will guide them towards this goal. If you’re not sure how to begin your list, I’ve included some ideas below that have worked well for my clients (and for me).

First of all, here are the top three traits women look for in a man: honesty, reliability, and his ability to communicate. In addition to these you might consider:

I can “be myself” when I’m with him.

I like how I feel when I’m around him.

He makes it obvious that my happiness and well-being are important to him.

He knows the difference between conversations and confrontations.

He is willing to make compromises.

He is warm and loving.

He makes me laugh.

He likes including me in other parts of his life.

Which of these “jump out” for you? If you get stuck making your list, ask a close friend to help – someone who knows your strengths and weaknesses well. Let the list be a “living” thing. Pull it out often to see if it still fits.

You’re on your way to proactively creating happiness for yourself in the New Year. If you’d like to share your list with us, we’d love to see it!

As I peruse online dating profiles some things women say puzzle me. Like one profile for a very appealing woman says “I love life.”
Eh?
Granted I’ve been accused of being too much in my head which I finally figured out means I analyze too much. Maybe I should just skip this sentence “I love life.”
But I can’t. Who doesn’t love living, considering the alternative…
I guess this woman is saying she’s happy which to me is very important. Does she look happy in her photos? This one definitely does. She’s smiling and in happy situations. Very appealing.
I like her. Maybe it’ because she loves life.

Joel: In response to a Facebook Friend who posted a list of attributes of a “Gentleman,” I posted this –

Glad to see this issue raised. I once listened to a woman in a singles group as she listed the (fairy tale) attributes of her ideal man.

When she finished, I asked, OK, so what do you bring to the table for him? After a long, long silence, she said, “Respect. I will respect him.”

To which I said, “Sorry, can’t use that. What behaviors and specific acts will you engage in to DEMONSTRATE your love; i.e., the kinds of things you listed that you know you want him to actually do for you, e.g. open the car door, etc.” (Please respond and you get extra points if you can use i.e. and e.g. in the same sentence, correctly!)

This is especially important for women looking for a mate so they can define limits and understand love is a two-way street, give and take, and, at best, giving more than you take… If you have a list of things you want from a man, put beside each item what you will actually DO for him to reciprocate.

Mind you, I like lists of things a woman wants. I have been and remain not naturally or instinctively sensitive in these matters. A woman I should have loved once, after a major fail, gave me a list she called “Minimum Expectations For Valentine’s Day.”

The next year I delivered. So… lists are good, just make sure you understand reciprocity.

Not a date but “The Graduate” illustrates age differences and difficulties in a relationship

Joel: When shopping on Match.com I searched for women within five years of my age. I thought we would be interested in the same things and have similar experiences. Maybe the music we love. Once I met a woman, we went out, I liked her and found out she was 10 years younger. I told her I worried about that. She said, “It’s always the older person who says that. I don’t care.”

Yeah, but… when I’m 80 she might feel differently. More importantly, will we have similar life experiences?

I’ve seen May-December couples who are happy so I’m sure it can work. But seems to me, especially since we get more and more locked in and resistant to change as we age, that closer in age is easier. I see many women post in their online profiles that they want a man their age or younger. When I asked women about that, they said it could be sex. “A lot of you old guys aren’t interested,” she said. Others said many men are couch potatoes.

The idea that resonated with me was that many women have been caretakers… children, an aging or sick husband, parents… they just don’t want to take care of anyone anymore. I get that, but it cuts both ways. You could be the one NEEDING care and that young guy would bolt when you tell him you have breast cancer.

Christine: Oh this is such a great subject Joel. Both the men and women I speak to in my practice often say they want to date someone their age or younger for the reasons you mentioned. In the past I used to hear “There are only jerky people using online dating.” And I’d say, “Gosh you don’t seem like a jerky person and you’re using online dating so there must be at least a few others like you. Don’t you think?” This often stopped them in their tracks. I’ve now found myself saying the same thing about the “age/health/activity level” that drive the comments about wanting to date someone younger.

My suggestion is if you’re active, don’t look or act your age and are using online dating it stands to reason there are more like you online. And if you’re not meeting people like you (and are instead meeting just the opposite) then consider what about you is attracting them or being attracted to them. Is it what you’ve written or not written in your profile? Is it the questions you ask or don’t ask during your initial communication with them? Try making some of these changes and see if you start meeting a different type of person online.

Also, don’t just depend on online dating. Get out and participate in activities that fit your lifestyle so you’ll be surrounded by “your kind of people doing you kinds of things.” (See Joel’s posting “Take A Hike“.)

I have dated men 10 years older and 10 years younger and I didn’t find either satisfying. There were always elements that are important to me missing because of the age difference. Even though sex was great with the men who were 10 years younger I got tired of having to explain my jokes that included themes they couldn’t relate to. When I dated men who were 10 years older we usually had very different goals for our futures. When I met and married my deceased husband one of the many things that was appealing to both of us was the two-year difference in our ages.